4-{2-[(5-Bromo-2-hydroxy-benzyl-idene)amino]eth-yl}benzene-sulfonamide.

In the title compound, C(15)H(15)BrN(2)O(3)S, the dihedral angle between the benzene rings is 6.1 (2)° and an intra-molecular O-H⋯N hydrogen bond helps to establish the conformation. In the crystal structure, the mol-ecules are linked by way of N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For related structures, see: Chohan et al. (2008 ▶, 2009 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H15BrN2O3S

M = 383.26

Orthorhombic,

a = 50.544 (6) Å

b = 6.3146 (10) Å

c = 4.8625 (5) Å

V = 1551.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.80 mm−1

T = 296 K

0.28 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.633, T max = 0.714

8263 measured reflections

2844 independent reflections

2523 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.100

S = 1.12

2844 reflections

213 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.79 e Å−3

Absolute structure: Flack (1983 ▶), 1212 Friedel pairs

Flack parameter: 0.050 (15)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809036083/hb5091sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036083/hb5091Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H15BrN2O3S	F(000) = 776
Mr = 383.26	Dx = 1.640 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2932 reflections
a = 50.544 (6) Å	θ = 2.4–28.3°
b = 6.3146 (10) Å	µ = 2.80 mm−1
c = 4.8625 (5) Å	T = 296 K
V = 1551.9 (3) Å3	Needle, yellow
Z = 4	0.28 × 0.14 × 0.12 mm

Bruker Kappa APEXII CCD diffractometer	2844 independent reflections
Radiation source: fine-focus sealed tube	2523 reflections with I > 2σ(I)
graphite	Rint = 0.035
Detector resolution: 7.80 pixels mm-1	θmax = 25.5°, θmin = 2.4°
ω scans	h = −52→60
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −7→6
Tmin = 0.633, Tmax = 0.714	l = −5→5
8263 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100	w = 1/[σ2(Fo2) + 2.7358P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max = 0.001
2844 reflections	Δρmax = 0.41 e Å−3
213 parameters	Δρmin = −0.79 e Å−3
1 restraint	Absolute structure: Flack (1983), 1212 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.050 (15)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Br1	0.24179 (1)	0.37198 (12)	1.16449 (17)	0.0633 (2)
S1	0.03204 (2)	−0.2434 (2)	−0.5033 (3)	0.0276 (3)
O1	0.15029 (7)	0.8114 (6)	0.6129 (10)	0.0543 (16)
O2	0.04542 (7)	−0.4313 (6)	−0.5921 (8)	0.0460 (12)
O3	0.02060 (7)	−0.1032 (6)	−0.7008 (7)	0.0398 (11)
N1	0.14244 (8)	0.4653 (8)	0.3341 (10)	0.0420 (16)
N2	0.00760 (8)	−0.3200 (7)	−0.3108 (12)	0.0367 (14)
C1	0.17777 (8)	0.5013 (8)	0.6554 (13)	0.0330 (14)
C2	0.17084 (9)	0.7071 (9)	0.7344 (10)	0.0360 (17)
C3	0.18524 (10)	0.8111 (9)	0.9375 (12)	0.0437 (19)
C4	0.20599 (10)	0.7116 (9)	1.0649 (10)	0.0403 (19)
C5	0.21316 (9)	0.5108 (9)	0.9871 (12)	0.0373 (16)
C6	0.19906 (10)	0.4058 (9)	0.7859 (11)	0.0397 (17)
C7	0.16276 (10)	0.3869 (9)	0.4471 (11)	0.0390 (17)
C8	0.12783 (10)	0.3344 (9)	0.1349 (13)	0.0463 (19)
C9	0.10328 (11)	0.2403 (10)	0.2692 (11)	0.0450 (19)
C10	0.08639 (10)	0.1205 (9)	0.0700 (9)	0.0330 (16)
C11	0.09253 (10)	−0.0829 (9)	−0.0103 (12)	0.0420 (19)
C12	0.07651 (10)	−0.1935 (8)	−0.1920 (12)	0.0380 (17)
C13	0.05431 (8)	−0.0959 (7)	−0.2953 (9)	0.0263 (16)
C14	0.04792 (10)	0.1065 (8)	−0.2252 (10)	0.0323 (17)
C15	0.06412 (10)	0.2172 (9)	−0.0426 (12)	0.0403 (17)
H1O	0.14259	0.73100	0.50732	0.0815*
H2A	−0.0025 (11)	−0.224 (8)	−0.292 (14)	0.0439*
H2B	0.0123 (10)	−0.405 (9)	−0.181 (13)	0.0439*
H3	0.18077	0.94875	0.98695	0.0522*
H4	0.21522	0.78030	1.20423	0.0481*
H6	0.20392	0.26884	0.73703	0.042 (16)*
H7	0.16828	0.25207	0.39564	0.06 (2)*
H8A	0.13916	0.22125	0.06878	0.0554*
H8B	0.12268	0.42041	−0.02147	0.0554*
H9A	0.10868	0.14594	0.41624	0.0540*
H9B	0.09291	0.35359	0.35006	0.0540*
H11	0.10770	−0.14723	0.05852	0.06 (2)*
H12	0.08071	−0.33135	−0.24312	0.030 (14)*
H14	0.03291	0.17034	−0.29820	0.040 (14)*
H15	0.06003	0.35623	0.00408	0.030 (13)*

	U11	U22	U33	U12	U13	U23
Br1	0.0515 (3)	0.0879 (5)	0.0505 (3)	0.0203 (3)	−0.0093 (4)	−0.0043 (4)
S1	0.0311 (6)	0.0282 (6)	0.0234 (5)	−0.0029 (5)	0.0027 (5)	−0.0059 (5)
O1	0.045 (2)	0.047 (3)	0.071 (3)	0.0065 (19)	−0.013 (2)	−0.008 (2)
O2	0.047 (2)	0.036 (2)	0.055 (2)	0.0026 (18)	0.0051 (19)	−0.0254 (19)
O3	0.047 (2)	0.042 (2)	0.0305 (18)	−0.0067 (19)	−0.0041 (16)	0.0036 (17)
N1	0.030 (2)	0.052 (3)	0.044 (3)	−0.010 (2)	−0.001 (2)	−0.009 (2)
N2	0.040 (2)	0.036 (3)	0.034 (2)	−0.0072 (19)	0.005 (3)	0.002 (2)
C1	0.028 (2)	0.034 (3)	0.037 (2)	−0.007 (2)	0.010 (3)	−0.009 (3)
C2	0.028 (3)	0.037 (3)	0.043 (3)	−0.004 (2)	0.008 (2)	−0.005 (2)
C3	0.042 (3)	0.036 (3)	0.053 (4)	−0.002 (2)	−0.002 (3)	−0.008 (3)
C4	0.040 (3)	0.046 (4)	0.035 (3)	−0.011 (3)	0.004 (2)	−0.009 (2)
C5	0.025 (2)	0.052 (3)	0.035 (3)	0.003 (2)	0.008 (2)	0.003 (3)
C6	0.038 (3)	0.037 (3)	0.044 (3)	−0.003 (3)	0.008 (2)	−0.008 (3)
C7	0.036 (3)	0.040 (3)	0.041 (3)	−0.006 (2)	0.007 (2)	−0.008 (3)
C8	0.042 (3)	0.057 (4)	0.040 (3)	−0.013 (3)	−0.011 (3)	−0.011 (3)
C9	0.046 (3)	0.051 (4)	0.038 (3)	−0.013 (3)	−0.005 (2)	−0.007 (3)
C10	0.031 (2)	0.041 (3)	0.027 (3)	−0.015 (2)	0.0053 (19)	−0.004 (2)
C11	0.034 (3)	0.047 (4)	0.045 (3)	0.003 (2)	−0.010 (3)	−0.004 (3)
C12	0.042 (3)	0.025 (3)	0.047 (3)	0.004 (2)	−0.007 (3)	−0.009 (3)
C13	0.031 (2)	0.028 (3)	0.020 (3)	−0.0034 (19)	0.004 (2)	−0.003 (2)
C14	0.030 (3)	0.028 (3)	0.039 (3)	−0.002 (2)	−0.002 (2)	−0.002 (2)
C15	0.045 (3)	0.034 (3)	0.042 (3)	−0.004 (2)	0.005 (3)	−0.011 (3)

Br1—C5	1.899 (5)	C9—C10	1.496 (8)
S1—O2	1.432 (4)	C10—C15	1.393 (7)
S1—O3	1.428 (4)	C10—C11	1.378 (8)
S1—N2	1.624 (5)	C11—C12	1.387 (8)
S1—C13	1.777 (4)	C12—C13	1.375 (7)
O1—C2	1.364 (6)	C13—C14	1.362 (7)
O1—H1O	0.8200	C14—C15	1.396 (7)
N1—C7	1.266 (7)	C3—H3	0.9300
N1—C8	1.472 (8)	C4—H4	0.9300
N2—H2A	0.80 (5)	C6—H6	0.9300
N2—H2B	0.86 (6)	C7—H7	0.9300
C1—C7	1.457 (8)	C8—H8A	0.9700
C1—C2	1.400 (8)	C8—H8B	0.9700
C1—C6	1.387 (7)	C9—H9A	0.9700
C2—C3	1.392 (7)	C9—H9B	0.9700
C3—C4	1.371 (7)	C11—H11	0.9300
C4—C5	1.372 (8)	C12—H12	0.9300
C5—C6	1.380 (8)	C14—H14	0.9300
C8—C9	1.523 (8)	C15—H15	0.9300
Br1···C6i	3.720 (5)	C7···C5vi	3.479 (7)
Br1···C4ii	3.433 (5)	C8···C1vi	3.594 (8)
Br1···C5ii	3.584 (5)	C13···O3i	3.356 (6)
Br1···H4iii	3.1700	C14···O3i	3.188 (6)
O1···N1	2.602 (6)	C15···O2x	3.259 (7)
O2···C15iv	3.259 (7)	C15···O3i	3.420 (7)
O3···N2v	3.076 (6)	C7···H1O	2.4200
O3···C14vi	3.188 (6)	C11···H8A	3.0600
O3···C15vi	3.420 (7)	H1O···N1	1.8800
O3···C13vi	3.356 (6)	H1O···C7	2.4200
O2···H12	2.5400	H2A···O3vii	2.30 (5)
O2···H15iv	2.4900	H2B···N2xi	2.70 (6)
O2···H9Biv	2.7700	H4···Br1xii	3.1700
O3···H14	2.6800	H6···H7	2.4500
O3···H2Av	2.30 (5)	H7···H6	2.4500
O3···H14v	2.7800	H7···H8A	2.1700
N1···O1	2.602 (6)	H8A···C11	3.0600
N2···O3vii	3.076 (6)	H8A···H7	2.1700
N1···H1O	1.8800	H9A···H11	2.5400
N2···H2Bviii	2.70 (6)	H9B···O2x	2.7700
C1···C4vi	3.470 (8)	H9B···H15	2.3600
C1···C8i	3.594 (8)	H11···H9A	2.5400
C4···C1i	3.470 (8)	H12···O2	2.5400
C4···C7i	3.526 (8)	H12···H15xiii	2.5400
C4···Br1ix	3.433 (5)	H14···O3	2.6800
C5···C7i	3.479 (7)	H14···O3vii	2.7800
C5···Br1ix	3.584 (5)	H15···O2x	2.4900
C6···Br1vi	3.720 (5)	H15···H9B	2.3600
C7···C4vi	3.526 (8)	H15···H12xiv	2.5400
O2—S1—O3	120.1 (2)	S1—C13—C12	119.3 (4)
O2—S1—N2	106.6 (2)	C12—C13—C14	121.5 (4)
O2—S1—C13	107.9 (2)	S1—C13—C14	119.0 (3)
O3—S1—N2	105.3 (2)	C13—C14—C15	119.4 (5)
O3—S1—C13	108.3 (2)	C10—C15—C14	120.3 (5)
N2—S1—C13	108.1 (2)	C2—C3—H3	120.00
C2—O1—H1O	109.00	C4—C3—H3	120.00
C7—N1—C8	118.2 (5)	C3—C4—H4	120.00
S1—N2—H2A	109 (4)	C5—C4—H4	120.00
S1—N2—H2B	114 (3)	C1—C6—H6	119.00
H2A—N2—H2B	124 (6)	C5—C6—H6	119.00
C2—C1—C7	121.4 (4)	N1—C7—H7	119.00
C6—C1—C7	120.4 (5)	C1—C7—H7	119.00
C2—C1—C6	118.2 (5)	N1—C8—H8A	110.00
O1—C2—C1	121.3 (5)	N1—C8—H8B	110.00
O1—C2—C3	118.5 (5)	C9—C8—H8A	110.00
C1—C2—C3	120.1 (5)	C9—C8—H8B	110.00
C2—C3—C4	120.3 (5)	H8A—C8—H8B	108.00
C3—C4—C5	120.1 (5)	C8—C9—H9A	109.00
Br1—C5—C4	120.2 (4)	C8—C9—H9B	109.00
Br1—C5—C6	119.6 (4)	C10—C9—H9A	109.00
C4—C5—C6	120.2 (5)	C10—C9—H9B	109.00
C1—C6—C5	121.1 (5)	H9A—C9—H9B	108.00
N1—C7—C1	122.0 (5)	C10—C11—H11	119.00
N1—C8—C9	110.2 (5)	C12—C11—H11	119.00
C8—C9—C10	112.6 (4)	C11—C12—H12	121.00
C9—C10—C15	119.6 (5)	C13—C12—H12	121.00
C11—C10—C15	118.6 (5)	C13—C14—H14	120.00
C9—C10—C11	121.8 (5)	C15—C14—H14	120.00
C10—C11—C12	121.2 (5)	C10—C15—H15	120.00
C11—C12—C13	118.9 (5)	C14—C15—H15	120.00
O2—S1—C13—C12	−16.3 (5)	C2—C3—C4—C5	1.9 (8)
O2—S1—C13—C14	168.7 (4)	C3—C4—C5—Br1	−179.7 (4)
O3—S1—C13—C12	−147.7 (4)	C3—C4—C5—C6	−1.9 (8)
O3—S1—C13—C14	37.2 (4)	Br1—C5—C6—C1	178.9 (4)
N2—S1—C13—C12	98.7 (4)	C4—C5—C6—C1	1.1 (8)
N2—S1—C13—C14	−76.4 (4)	N1—C8—C9—C10	175.1 (5)
C8—N1—C7—C1	−177.3 (5)	C8—C9—C10—C11	79.5 (7)
C7—N1—C8—C9	101.1 (6)	C8—C9—C10—C15	−99.3 (6)
C6—C1—C2—O1	179.3 (5)	C9—C10—C11—C12	179.0 (5)
C6—C1—C2—C3	0.4 (8)	C15—C10—C11—C12	−2.2 (8)
C7—C1—C2—O1	−2.2 (8)	C9—C10—C15—C14	−179.0 (5)
C7—C1—C2—C3	178.8 (5)	C11—C10—C15—C14	2.3 (8)
C2—C1—C6—C5	−0.4 (8)	C10—C11—C12—C13	0.8 (8)
C7—C1—C6—C5	−178.8 (5)	C11—C12—C13—S1	−174.3 (4)
C2—C1—C7—N1	−2.0 (8)	C11—C12—C13—C14	0.6 (8)
C6—C1—C7—N1	176.4 (5)	S1—C13—C14—C15	174.4 (4)
O1—C2—C3—C4	179.9 (5)	C12—C13—C14—C15	−0.5 (7)
C1—C2—C3—C4	−1.2 (8)	C13—C14—C15—C10	−1.0 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1	0.82	1.88	2.602 (6)	147
N2—H2A···O3vii	0.80 (5)	2.30 (5)	3.076 (6)	163 (5)
C15—H15···O2x	0.93	2.49	3.259 (7)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N1	0.82	1.88	2.602 (6)	147
N2—H2A⋯O3i	0.80 (5)	2.30 (5)	3.076 (6)	163 (5)
C15—H15⋯O2ii	0.93	2.49	3.259 (7)	140

Symmetry codes: (i) ; (ii) .